The Rebooting Show

Alex Kantrowitz is the founder of Big Technology, an independent publication focused on he immense impact of tech companies on business, politics and society. A reporter covering tech for BuzzFeed News, he wrote a book on the tech industry called “ Alw...

Semafor, backed by $25 million in private investment, has (finally) launched, marking possibly the most ambitious attempt in recent years to build a new global news brand. At the heart of the effort is an attempt to restore trust in media by rethinking...

6am City is turning to the newsletter to build out a network of 25 local news publications it says have 1 million cumulative subscribers and an open rate around 50%. After starting in Greenville, South Carolina, in 2016, 6am has expanded to markets lik...

In 2014, Bonnie Kintzer was named CEO of Readers Digest Association, becoming its fourth CEO in three years as it emerged months earlier from its second bankruptcy. After renaming the company Trusted Media Brands, recently shortened to TMB, Bonnie set ...

Casey Newton, a former writer at The Verge, started Platformer to cover the societal impact of the most powerful tech platforms. He’s used a subscription model, charging $100 a year. With 75,000 free subscribers and what he’ll only call “thousands” of ...

This is a preview of a new weekly podcast I’m doing with Troy Young. The People vs Algorithms podcast will focus on patterns in media, business and culture. Each episode will revolve around themes. This week, we tackled the theme of whether media is be...

Flying, a 95-year-old magazine publisher focused on amateur pilots, is on this path. Craig Fuller, CEO of Freightwaves, bought Flying in July 2021 and a key part of the growth plan he and COO Preston Holland have begun is a massive bet on so-called air...

Future is a collection of over 200 specialist titles that range from gaming and tech (Tech Radar) to homes (Homes & Garden) to beauty and fashion (Who What Wear) to B2B (SmartBrief), Future has established itself as one of the UK’s most successful publ...

The business of hip hop is often overlooked, even though it's a massive business with outsized cultural influence. Dan Runcie saw this as an opportunity, starting Trapital in 2018. I wanted to talk to Dan about his approach to building an independent m...

Begun as a meme account in 2017, Litquidity has amassed 1 million social media followers across Instagram, Twitter, LinkedIn and TikTok, specializing in the dark arts of “dank memes” that poke fun at the weird world of finance. The account, run pseudon...

In February 2021, marketing software company HubSpot bought popular business newsletter The Hustle. Jordan DiPietro, a veteran of The Motley Fool, joined HubSpot to run The Hustle just after the acquisition, after having spent time advising the company...

One of the most solid areas of digital publishing is what’s become known as intent media. In the old days, we called this “SEO.” The basics are taking service content and applying it to algorithmic distribution (usually Google) and marrying it with per...

Adam Ryan, former president of The Hustle and cofounder of Workweek, wants to rethink the B2B model. Workweek is banking on finding individuals – creators, if you will – to build audiences around. The bet is that individuals, particularly but not exclu...

The pendulum always swings. Media regularly oscillates between periods of bundling and periods of unbundling. Bundles tend to rub people the wrong way because they feel they pay for stuff they don’t want. The downside is unbundling can be a complete ha...

Everyone loves a comeback, but few companies get them in the consumer internet business. (Most companies have peaked and then set course on inevitable decline, with new owners either milking the asset on the way down or floundering unsuccessfully to re...

Katie Vanneck-Smith, formerly president of Dow Jones, co-founded Tortoise Media, a UK-based publisher dedicated to “slow news.” The problem she and her co-founders diagnosed: “The problem isn’t just fake news or junk news, because there’s a lot that’s ...

Outsider is a media and commerce brand focused on a particular view of “the American lifestyle” that, to me, takes its cues from the South, emphasizing college football, hunting, fishing, wraparound sunglasses and the like. Recently, Deirdre Lester mov...

The crypto winter has pitched the giddy excitement over the endless possibilities of Web3. The drumbeat of negativity hasn’t shaken Time president Keith Grossman’s confidence in Web3 providing a new path to sustainable business models. Time, now under ...

Morning Brew is a breakout success in digital media, turning an email newsletter of business news delivered with a witty tone, into a robust digital media business that now has over 4 million email subscribers, with another 1 million to its growing sta...

Since its founding eight years ago, Permutive has bet on privacy being a key consideration in the future of ad tech. Permutive CEO Joe Root delves into what privacy-conscious advertising looks like – and if it’s possible. Highlights: The GDPR was a har...

Forbes is a unique brand that has global cultural cachet that’s managed the transition from being a magazine business to a mostly digital business, with an emphasis on building its direct revenue as well as its brand extensions. Now, it's looking to pl...

Why The Dispatch outgrew Substack Many would assume the most popular political publications on Substack are culture war agitators like Matt Taibbi and Glenn Greenwald. In fact, the top two slots are much milder publications: Letters from an American an...

Quick request: Please take this 10-question audience survey that will help me better understand the makeup of The Rebooting’s readership in order to grow it as a sustainable business. I’ve already gotten many useful insights from the first wave of resp...

I decided to mix up the days for this newsletter and the format. You’ll now get The Rebooting twice a week, Tuesday and Thursday. The Tuesday email will continue with a new format that is a mix of topics, along with highlights from the podcast. I think...

The future of work is one of the most fertile topic areas out there. The pandemic caused a reset, when combined with the labor shortage coming out of Covid, and it’s not going back to normal. The Atlantic’s Derek Thompson cited statistics that show bas...

Check out the full episode on Apple Podcasts or Spotify. Let me know what you think: [email protected]. The war in Ukraine is now six weeks old, likely to drag on even longer. It’s important to consider how vital an independent and free media is to ...

Welcome to new subscribers. One way to support The Rebooting is by sharing it with colleagues and friends you think would find it valuable. I still view The Rebooting Show, as well as the overall project, as a work in progress, so please let me know gu...

On this week’s episode of The Rebooting Show, I spoke to Skift CEO Rafat Ali. What I like about Skift is it goes narrow and deep on the business of travel while situating it within the broader context of the global economy and societal trends. Covid wa...

Something about the podcast highlights format wasn’t working for me, so I’m switching up the Monday version to feature highlights from the podcast as well as some thoughts on other matters in sustainable publishing. After all, formats matter. Let me kn...

Subscribe on Apple Podcasts and Spotify If you use Apple, please leave a rating and review. Every cycle of unbundling is followed by another period of rebundling. Media is no different – just look at the streaming market. In publishing, the shift of po...

Subscribe on Apple Podcasts and Spotify If you use Apple, please leave a rating and review. Journalists in their 40s are under no illusions to the need for sustainable business models in news publishing. Being suddenly laid off is a rite of passage. “T...

Subscribe on Apple Podcasts and Spotify Like just about everyone, I’m both horrified by the Russian invasion of Ukraine and in awe of the resistance of the Ukrainian people. Ukraine is an inspiration to the rest of the world. In places like the United ...

Subscribe on Apple Podcasts and Spotify Over just five years, crypto has exploded from a curiosity to a cultural touchstone, with millions of boosters, Super Bowl commercials and billions of investment in the belief that a new financial system, built f...

Subscribe on Apple Podcasts and Spotify Apple users: Please l eave a rating and review. When it comes to business models, software models beat publishing ones. Recurring revenue scales more quickly and at far better margins. For a decade, Famous Birthd...

Welcome to this week’s edition of The Rebooting Show. This week’s episode is a sponsored Spotlight episode, where I feature a conversation with a sponsor of The Rebooting in order to get a better understanding of their approach to solving a challenge o...

This week I’m continuing a run of discussions with people operating the publications that sit at the nexus of power and politics. Punchbowl has had a successful launch as one of the new crop of publishers. Check out the episode, and if you’re not alrea...

Subscribe on Apple Podcasts and Spotify The roaring 20s of publishing has begun with several new brands launching, each with their own twist on dealing with the challenges of audience growth and sustainable business models. What’s notable is most publi...

Thanks to everyone who has sent notes and left reviews for the podcast on Apple Podcasts. Thanks to Jrdoog, who called the podcast “essential for anyone working in the media industry.” Note for future guests: Jrdoog wants me to keep badgering you for n...

Subscribe on Apple Podcasts and Spotify I’m continuing my look-ahead series of podcast episodes to kick off 2022. Last week, Sara Fischer, media reporter for Axios, laid out her big themes for the year. This week, I spoke to Troy Young, the former pres...

Subscribe on Apple Podcasts and Spotify Hope everyone’s 2022 is off to a good start. I’m kicking off a new mini-season of episodes this month that will focus on what to expect this year in digital media. To start, I spoke with Axios media reporter Sara...

Subscribe on Apple Podcasts and Spotify Happy holidays. I’m wrapping up the year with a final podcast and then, on Wednesday, I’ll send out the second annual Rebooting Awards. In the meantime, my final podcast of the year is with Rishad Tobaccowala, a ...

Subscribe on Apple Podcasts and Spotify What a strange end to the year, with Omicron the march, inflation jitters and more unknowns than seemingly ever before. But there’s not the same amount of panic and anxiety as the spring 2020 — positive Covid tes...

Subscribe on Apple Podcasts and Spotify This week, I’m wrapping up the first mini-season of The Rebooting Show. This season was dedicated to modern B2B businesses. If you haven’t already, please check out the first four episodes of the season: Adam Whi...

Subscribe on Apple Podcasts and Spotify This week’s episode of The Rebooting Show features a conversation I had with one of my favorite media success stories: Industry Dive, a collection of vertical industry sites. Sean and his team have grown Industry...

Subscribe on Apple Podcasts and Spotify For episode 3 of The Rebooting Show’s mini-season focused on modern B2B media, I spoke to Angus Macaulay, COO of Stat, the health-focused site that’s one of my favorite niche media brands. Please send me an email...

Subscribe on Apple Podcasts and Spotify Thanks for the notes following the debut of The Rebooting Show. You can subscribe now on both Apple and Spotify. We’re working hard to improve the audio quality, and I’m going to make sure the episodes get shorte...

Subscribe on Apple Podcasts — more platforms coming soon. After a year break from podcasting, I’ve finally started anew with The Rebooting Show, a weekly audio and video discussion that goes into the details of building sustainable media businesses wit...